EP 1961725 A1 20080827 - Odorous and aroma substances, their manufacture and utilisation
Title (en)
Odorous and aroma substances, their manufacture and utilisation
Title (de)
Riech- und Aromastoffe, ihre Herstellung und Verwendung
Title (fr)
Arômes, parfums, leur fabrication et utilisation
Publication
Application
Priority
EP 07103066 A 20070226
Abstract (en)
(5-Isopropylidene-2-methyl-cyclohexyl)-methanol compound and its enantiomer, preferably two or more mixture of (1S, 2S)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol, (1S, 2R)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol, (1R, 2S)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol and (1R, 2R)-(isopropyliden-2-methyl-cyclohexyl)-1-methanol, is new. (5-Isopropylidene-2-methyl-cyclohexyl)-methanol compound of formula (I) and its enantiomer, preferably two or more mixture of (1S, 2S)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol, (1S, 2R)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol, (1R, 2S)-(isopropylidene-2-methyl-cyclohexyl)-1-methanol and (1R, 2R)-(isopropyliden-2-methyl-cyclohexyl)-1-methanol, is new. Independent claims are included for: (1) a perfume or aroma material mixture comprising (I) and its enantiomer and one or more further perfume or aroma material, which has a woody and/or a flowery smell and/or taste; (2) a perfumed and/or an flavored article comprising the perfume- or aroma material mixture; (3) preparing (I) comprising either converting 4-isopropylidene-1-methyl-cyclohexene (A) to a (5-isopropylidene-2-methylene-cyclohexyl)-methanol compound of formula (IV) by a Prins-reaction and subsequently selectively, catalytically, hydrogenating (IV) to give (I) or reducing (5-isopropylidene-2-methyl-cyclohexyl)-carbaldehyde (B) to give (I) or converting (5-isopropylidene-2-methyl-cyclohexyl)-carbonitrile (C) to 5-isopropylidene-2-methyl-cyclohexanecarboxylic acid (D) and subsequently reducing (D) to (I), where (B) is produced by converting (A) by hydroformylation or reducing (C); (4) (5-isopropylidene-2-methyl-cyclohexyl)-carbonitrile (C) and its syn- and anti-enantiomer; and (5) preparing (5-isopropylidene-2-methyl-cyclohexyl)-carbonitrile (C) comprising carrying out a Michael-addition with subsequent aldol condensation of but-3-en-2-one and propionaldehyde to give 4-methyl-cyclohex-2-enone, adding hydrogen cyanide to 4-methyl-cyclohex-2-enone to give 2-methyl-5-oxo-cyclohexanecarbonitrile and converting 2-methyl-5-oxo-cyclohexanecarbonitrile in Wittig-reaction to give (C). [Image] [Image].
Abstract (de)
Die vorliegende Erfindung betrifft Verbindungen der Formel (I) , ihre Verwendungen als Riech- oder Aromastoff, ihre Herstellung, Artikel enthaltend diese Verbindungen und Verfahren zum Vermitteln, Modifizieren und/oder Verstärken eines blumigen und/oder rosigen Geruchs oder Geschmacks. Die Erfindung betrifft ferner (5-Isopropyliden-2-Methyl-Cyclohexyl)-Carbonitril und Verfahren zu dessen Herstellung. (5-Isopropyliden-2-Methyl-Cyclohexyl)-Carbonitril ist insbesondere geeignet als Zwischenprodukt bei der Herstellung von Verbindungen der Formel (I).
IPC 8 full level
A61K 8/34 (2006.01); C07C 33/14 (2006.01); C07C 255/46 (2006.01); C11B 9/00 (2006.01)
CPC (source: EP)
C07C 29/17 (2013.01); C07C 33/14 (2013.01); C07C 255/46 (2013.01); C11B 9/0034 (2013.01); C07B 2200/07 (2013.01); C07C 2601/14 (2017.04)
Citation (search report)
- [A] DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; GORA, JOZEF ET AL: "Method for manufacturing ethyl menthoxyacetate as a fragrance", XP002444611, retrieved from STN Database accession no. 1991:43241
- [A] DATABASE WPI Week 198939, Derwent World Patents Index; AN 1989-282548, XP002444614
- [A] SEMMLER, F. W. ET AL: "Constituents of Ethereal Oils. Constitution of Perillaldehyde, C10H14O", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 44, 1911, pages 52 - 7, XP002447907
- [A] RYKOWSKI ET AL: "Reaction of (+)-dihydroxycarveol tosylate with KCN in aprotic solvents, (-)-(1S,2R,4S)-1-methyl-4-isopropenylcyclohexane-2-carbonitril", ANNALES UNIVERSITATIS MARIAE CURIE-SKLODOWSKA. SECTIO AA. CHEMIA, WYDAWNICTWO UNIWERSYTETU MARII CURIE-SKLODOWSKIEJ W LUBLINIE,, PL, vol. 48-49, no. 9, 1993, pages 137 - 147, XP009087525, ISSN: 0137-6853 & PL 150119 B2 19900430
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR
Designated extension state (EPC)
AL BA HR MK RS
DOCDB simple family (publication)
DOCDB simple family (application)
EP 07103066 A 20070226